Last Updated: January 22, 2022
Grappling has been a staple tactic of clever players since 5th edition’s release, and has existed for decades in prior editions of Dungeons and Dragons. The ability to hold foes in place (especially while they’re prone) can be a powerful advantage, and having a capable grappler in the party can be a huge asset.
In this article we’ll explore the rules of grappling, do a little bit of math, and look at ways that you can both make grappling work for you and handle the inevitable situation where an enemy grapples you.
Table of Contents
- The Rules
- Optimizing For Grapples
- Countering Grapples
RPGBOT uses the color coding scheme which has become common among Pathfinder build handbooks, which is simple to understand and easy to read at a glance.
- : Bad, useless options, or options which are extremely situational. Nearly never useful.
- : OK options, or useful options that only apply in rare circumstances. Useful sometimes.
- : Good options. Useful often.
- : Fantastic options, often essential to the function of your character. Useful very frequently.
I will not include 3rd-party content, including content from DMs Guild, even if it is my own, because I can’t assume that your game will allow 3rd-party content or homebrew. I also won’t cover Unearthed Arcana content because it’s not finalized, and I can’t guarantee that it will be available to you in your games.
The advice offered below is based on the current State of the Character Optimization Meta as of when the article was last updated. Keep in mind that the state of the meta periodically changes as new source materials are released and this article will be updating accordingly as time allows.
RPGBOT is unofficial Fan Content permitted under the Fan Content Policy. Not approved/endorsed by Wizards. Portions of the materials used are property of Wizards of the Coast. ©Wizards of the Coast LLC.
As with any set of rules, understanding the rules well is key to getting the most out of using those rules. To that end, let’s take a look at the rules text from the SRD and make sure that we understand exactly what it all means.
We’ll need to look beyond the Grapple rules, too, so settle in. Once you’ve gotten your head around this you’ll hopefully never need to read this section again, but I promise that it’s worth your time. And if you DM ever looks at you and says “it can’t possibly work like that”, point them here.
When you want to grab a creature or wrestle with it, you can use the Attack action to make a special melee attack, a grapple.
This tells us some important things:
- Grappling uses the “Attack” action, and is not its own action
- It is a “special melee attack” which means that it’s done in melee (so you can’t grapple from 30 feet away), and since it’s an attack it interacts with other rules that care about attacks, such as the Barbarian’s Rage and the Invisibility spell.
- Because grappling is done with the Attack action, you can’t grapple as an Opportunity Attack.
If you’re able to make multiple attacks with the Attack action, this attack replaces one of them.
Very import for martial characters likely to rely on grappling, this means that if you have Extra Attack you can grapple and still make other attacks using the same Attack action.
The target of your grapple must be no more than one size larger than you…
This part is easy to overlook, but extremely important. A small creature can only grapple creatures of up to medium size, so your gnome barbarian is going to struggle against big chunks of the Monster Manual. As a result, grapple builds should expect to include a medium race.
…and must be within your reach.
Note that this is your character’s reach, not the reach of their weapon. You can’t grapple using a whip or a glaive or whatever.
Using at least one free hand…
Extremely important. If you typically fight with a “sword and board” arrangement (meaning a weapon and a shield), grappling is difficult. However, if you fight unarmed to even using a two-handed weapon, you have a free hand most of the time with which you can attempt a grapple.
Strangely, after you start the grapple, there’s no requirement to keep that hand free. You’re free to use that hand to go back to attacking with a two-handed weapon or to grapple a different creature.
This also means that creatures without hands can’t initiate a grapple unless they have some other way to do so. For example: a giant toad has no hands, but if they hit a creature with their bite, the target is grappled. This notably doesn’t require a check and doesn’t care about size; it simply happens.
…you try to seize the target by making a grapple check instead of an attack roll: a Strength (Athletics) check…
Instead of an attack roll, you make an ability check to initiate a grapple. This tells us that, at the very least, if you want to grapple you need decent Strength and proficiency in Athletics. This means that you’re unlikely to see many wizards grappling, but barbarians, fighters, and paladins should do fine.
…contested by the target’s Strength (Athletics) or Dexterity (Acrobatics) check (the target chooses the ability to use).
This is an important point for creatures attempting to resist grapples. Not every creature is immensely strong, but many are nimble, wiggly, or otherwise difficult to restrain, and either set of capabilities can help you get out of a grapple.
Offensively, this means that grapplers will want to pick targets who are bad at both Acrobatics and Athletics. Grappling ogres or quicklings may be hard, but grappling wizards is typically easy. Defensively, this means that melee builds may want a way to escape grapples, typically by being proficient in either Acrobatics or Athletics depending on which of their Strength or Dexterity is higher.
If you succeed, you subject the target to the grappled condition. The condition specifies the things that end it…
The Grappled condition is why you want to start a grapple. It’s a little bit complicated, so we’ll examine the Grappled Condition below.
and you can release the target whenever you like (no action required).
“Whenever you like” seems to indicate that it doesn’t need to be on your turn, especially since it doesn’t require an action. If you’re unable to take actions for some reason, but that reason doesn’t also break the grapple, it looks like you can still choose to release the target.
Escaping a Grapple
Once a creature is grappled, they’ll frequently want to stop being grappled. You can still fight in melee while grappled without too much trouble, but not every creature likes to stand still and kick things in the shins until their hit points drop to 0, so sometimes you need to escape a grapple.
A grappled creature can use its action to escape.
Escaping a grapple takes an Action. Considering that it takes an attack (which might be one of several taken with the Attack action, or might just grapple the target as a secondary effect) to start a grapple, the action economy is heavily in the attacker’s favor.
That imbalance in the action economy is one of the reasons why players like to grapple offensively, but also why players try really hard to get out of grapples by any other means possible. See Countering Grapples, below.
To do so, it must succeed on a Strength (Athletics) or Dexterity (Acrobatics) check contested by your Strength (Athletics) check.
These are the same ability checks used to initiate and to resist a grapple. That consistency in the rules is nice because it’s to remember what you need to do.
The Grappled Condition
You did it! You grappled something! Or something grappled you! I don’t know, I’m not your DM. Either way, you need to know what that means for whoever is grappled.
A grappled creature’s speed becomes 0, and it can’t benefit from any bonus to its speed.
Reducing a creature’s speed to 0 is the entire point of grappling them. The primary benefit is that they can’t run away, but importantly if your speed is 0 you can’t do anything which requires expending some portion of your move speed. For example: you can’t stand up (see Shove, below) and you can’t mount or unmount a horse.
The target also can’t benefit from bonuses to speed, so things like Longstrider or Haste don’t magically let you walk out of a grapple.
Having a creature’s speed reduced to 0 is already a significant benefit if you go no further. Having allies place ongoing damage effects like Create Bonfire or Cloud of Daggers is easy damage output at minimal cost, making your whole party more efficient and effective.
The condition ends if the grappler is incapacitated (see the condition).
Incapacitated is an important condition, and in addition to being a condition on its own it’s also applied by other conditions like paralyzed and unconscious. So you can end a grapple by paralyzing the grappler, putting them to sleep, and a whole bunch of other things.
The condition also ends if an effect removes the grappled creature from the reach of the grappler or grappling effect, such as when a creature is hurled away by the thunderwave spell.
Getting the grappler and the grappled creature apart is typically the easiest and most efficient way to break a grapple. Thunderwave is an excellent and easily-understood example, but you can also use teleportation, or you can just Shove the grappler away.
The Bugbear race has a weird edge case here: The long-limbed trait extends your reach for melee attacks on your turn by 5 feet. This means that you could initiate a grapple (grapple is a melee attack), but if the grappled creature is then outside of your reach after the attack, the grapple immediately ends.
Moving a Grappled Creature
While a grappled creature has its speed reduce to 0, the creature who initiated the grapple has no such problem. Sometimes, as a grappler, you may want to move the grappled creature somewhere else, such as by dragging them into a wall of fire or tossing them into a pit. This is frequently a more efficient way to reposition a creature than by using Shove, so understanding how it works is very helpful for front-line martial characters even if you don’t grapple frequently.
When you move, you can drag or carry the grappled creature with you, but your speed is halved…
Useful, but vague.
There’s no clear explanation about what “drag” means here, so we’re left to fill in the meaning using plain English. “Drag” means to pull, so you can’t push the target away by grappling them (though maybe you could by carrying them?). There’s also no rules about where the creature is positioned, so you’ll need to work it out with your DM on a case-by-case basis.
Carrying a grappled creature is even less clear. If you’re a human grappling an ogre, how are you supposed to carry them? Can you pick them up, carry them to a window, then drop them out of it? I honestly have no idea.
As a DM, I try to interpret these rules as simply as possible. When you move while grappling a creature, any creatures remain in the same position relative to your space, so they basically “float” in space as you move.
These rules also don’t seem to care how many creatures you have grappled, so if you grapple numerous foes (or any creature really, since you can technically grapple allies) you’re free to drag them all around at the same time.
The rules also don’t care about what sort of movement you use, and Jeremy Crawford has tweeted that it works with movement of any sort. This means that you could grapple creatures then fly into the air, drag them up walls with a climb speed or spider climb, or if you’re a monk potentially even run up a wall while grappling a creature. This both discourages creatures from breaking the grapple and gives you an easy source of additional damage output when you inevitably decide to drop them.
Since I get this question frequently: These rules don’t care about a creature’s actual weight, so the carrying capacity rules do not matter here. The Monster Manual doesn’t specify creatures’ weights, and you options in a grapple shouldn’t hinge on whether or not the target has had a heavy lunch.
unless the creature is two or more sizes smaller than you.
A medium creature could grapple a tiny creature such as a pixie or a house cat and drag them around without any impact on your speed. If you become large, you can do the same for small creatures like halflings.
While it’s not part of the Grapple rules, the rules for Shoving a Creature are frequently used in combination with grappling. Shoving a Creature allows you to shove a creature prone. When combined with the Grappled condition, this prevents creatures from standing (you can’t expend movement when your speed is 0, and standing requires expending half of your movement).
This is frequently referred to as the grapple+shove combo, and it’s a powerful tactic for martial characters. Forcing enemies to remain prone is an easy way to get Advantage on attacks, and a character optimized for grappling already has everything that they need to Shove, too. This is typically the most useful way to consistently benefit from grappling in combat, so I’ll refer to the grapple+shove combo repeatedly throughout this article.
Note that your allies will also be affected by you shoving creatures prone. Other melee attackers will benefit, while allies relying on ranged attack rolls (archers, warlocks, etc.) will suffer Disadvantage to hit the target. If your ranged allies complain about you knocking foes prone, encourage them to learn spells like Create Bonfire or to switch targets.
While this is an edge case, you can grapple or shove in the same turn that you use Two-Weapon Fighting, provided that you have Extra Attack. To perform two-weapon fighting, you need to take the Attack action and attack with a qualifying weapon. However, you only need to make that attack once, so if you have Extra Attacks you could spend any additional attacks to grapple and/or shove (remember that they’re “special melee attacks”). However, since you need a free hand to grapple you may need to either throw or drop one of your weapons.
Climbing a Creature
An optional rule presented in the Dungeon Master’s Guide, the Climbing a Creature rule allows creatures to use rules similar to Grapple and Shove to climb the creature, granting your Advantage on attacks against the creature that you’re climbing. While this optional rule is far from perfect, it’s a great way for grapple builds to remain relevant when facing creatures that are too large to grapple, potentially even allowing small races to produce successful grapple builds.
Optimizing For Grapples
Optimizing for grappling, including the grapple+shove combo, isn’t especially difficult, but there’s a lot to consider, and the further you go the more effective you’ll be.
I recommend addressing the following points in this order.
- Strength. A crucial part of the formula, especially at low levels before your Proficiency Bonus scales. An optimized grappler will typically start with a +3 Strength modifier.
- Proficiency. Proficiency and Expertise in Athletics are the most mathematically impactful thing that you can do to improve your grappling. If you can get Expertise, such as from levels in rogue or from the Skill Expert feat, that will have a huge impact, especially as your Proficiency Bonus scales with level.
- Extra Attack. The ability to make multiple attacks in the same turn means that you can grapple and shove in the same turn, which gets the grapple+shove combo working in one turn rather than two, doubling your effectiveness.
- Size. You can only grapple creatures up to one size larger than you, so if you want to grapple everything you meet, you’ll want to be as large as possible. The Climbing a Creature optional rule can make this point less crucial, but only if you’re okay with whatever you’re grappling walking around while you climb all over it.
- Advantage. Advantage works out to slightly more than +3, but your Strength modifier can almost match that right at level 1, and your Proficiency Bonus will scale with level, especially if you have Expertise and are doubling your Proficiency Bonus, which is why those points are more crucial.
- Imposing Disadvantage. Typically harder than finding a way to get Advantage, imposing Disadvantage on your target is just as impactful. Spells like Hex can provide consistent, easy ways to accomplish this.
- Other Stuff. Other sources of bonuses for yourself and penalties for your targets are less common and often less permanent, but they can still have a useful benefit to improve your grappling. Examples includes things like Guidance, the Grappler feat, and Fighting Style (Unarmed).
I consider 1 through 4 the essentials, but more is always better. Other people may disagree with me regarding what should be considered “essential”, and that’s fine. I consider 1-4 essential because they are typically permanent parts of your character, while Advantage/Disadvantage are frequently circumstantial, temporary, or constrained by limited resources like daily uses of Rage or spell slots.
Your choice of race is fairly simple. At the very least, you want a medium race with a Strength increase, and that’s
- : Unfortunately, the Powerful Build feature doesn’t help you with grapples, so races with Powerful Build don’t get any benefit. The grapple rules care about creature size, not your actual carry weight.
- TCoE: +2 Strength and a feat. Grab Skill Expert and you can get another +1 Strength and both proficiency and expertise and Athletics. That gives you a +8 Athletics modifier at level 1 regardless of your class if you start from a base of 15 Strength, beating every other race’s best possibly modifier at level 1. That advantage will go away once every build can hit 20 Strength, but at low levels it’s really nice.
- PHB. Can cast Enlarge/Reduce to become large, but you can’t re-cast it using spell slots.
- WBtW: Flight and you can cast Enlarge/Reduce to make yourself large. Unfortunately, at small size you’ll absolutely need Enlarge to function, which creates a persistent and problematic tax on your resources and action economy.
- VGtR: A good option for any build that will have spellcasting since you get Hex and can re-cast it using spell slots..
- VGtR: Knowledge From a Past Life can save you in a pinch if you fail an Athletics check by one or two, but it’s not enough on its own to make your build good. File this one under “Other Stuff”.
- PHB: Custom Lineage is strictly better if you’re going for Skill Expert, but if you’re going for Expertise from another source, Variant Human may be better depending on your build.
Your class is the only thing that can give you Extra Attack, which makes your class extremely important. Different race/class combinations can get you to roughly the same place, so if your race choice supports your build very well, your class options can be more flexible without sacrificing effectiveness.
- : The Armorer and the Battle Smith both get heavy armor and Extra Attack, and the Artificer can cast spells like Guidance and Enhance Ability. Building an artificer around Strength would be exceptionally weird, but you get a lot from one class, so if you can make room for Skill Expert (easy for Custom Lineage or Variant Human), you’re in good shape. Proficiency in Constitution saves makes it easy to maintain Concentration on spells, too.
- : Rage is among the easiest ways to get Advantage on Strength checks, which includes Athletics. A Custom Lineage or Variant Human can get you Skill Expert in Athletics, but if you don’t start with a feat a single level of rogue will do the trick, too. At level 20 you can get up to 24 Strength, which no one else can do without magic items. A durable subclass like Path of the Ancestral Guardian or Path of the Totem Warrior makes it easy to focus on holding foes in place while your allies kill them, and Path of the Storm Herald’s Desert aura can apply repeated damage to enemies held in the area by your grapple.
- : Bards can cast Guidance, Borrowed Knowledge, and Enhance Ability, and they get Expertise. College of Valor gets Extra Attack. If it wasn’t so difficult to build a Strength-based bard, they would be a decent option. If you take a feat or a class dip to get heavy armor proficiency, this could work.
- : Only circle of the moon druids should grapple, and when they do so, they should use a form with an attack that grapples on a hit. Unfortunately, while using Wild Shape your own skill modifiers don’t apply and you typically don’t have hands to initiate a grapple using the normal way, so few of the typical optimization tricks apply. Applying Disadvantage can still keep enemies from escaping your grapple, but that can be hard to accomplish without help while using Wild Shape. You could cast Hex before you jump into Wild Shape, but maintaining Concentration is often difficult due to your forms’ typically low AC and relatively poor stats.
- : Unfortunately, monks are built around Dexterity, so they’re typically terrible at grappling. Way of the Astral Self presents an exception by allowing you to grapple using Wisdom, and you can do so with 10-foot reach, which most grapplers can’t replicate. You also get Extra Attack.
- : The best version of Extra Attack, going up to 4 attacks with a single Action before you consider Action Surge. The Fighter is the only class that gets Unarmed on their list of Fighting Style options, and while d4 damage isn’t great it’s still a nice addition to a grapple builds. The Eldritch Knight can cast buffs like Enlarge/Reduce to get Advantage on Strength checks and raise your size to large, and the Rune Knight’s Giant’s Might grants Advantage on Athletics Checks and can get you up to Huge size at high levels, allowing you to grapple anything in the game.
- : The Paladin gets Extra Attack, so if you can get Expertise in Athletics elsewhere you have the essentials. Oath of Glory’s Channel Divinity (Peerless Athlete) can get you Advantage without consuming Concentration.
- : The Optional Class Feature Canny gives the ranger Expertise in one skill at first level and the Ranger gets Extra Attack, making them the only class other than the Bard which can get both of those essentials without multiclassing. You also get a Fighting Style, but tragically Unarmed is only available to fighters or via the Fighting Initiate feat. If you’re planning a class dip to get Expertise, the Rogue is a better choice. But a Strength-based grappler ranger can absolutely work.
- : Expertise at first level. This is an easy multiclass dip if you don’t get Expertise from a feat, but rogues don’t get Extra Attack so they don’t make effective grapplers as a single-class build.
- : You can cast Hex, but that’s basically all that you get. Two levels for an extra spell slot or three for Pact of the Chain (a familiar can take the Help action to give you Advantage), are tempting, especially once you’ve got the essentials. Keep in mind that Thirsting Blade is not Extra Attack, so an all-warlock build won’t do the trick.
- TCoE: Take this to get Fighting Style (Unarmed). It’s not essential, and the 1d4 damage never scales, but it can add up if you grapple multiple creatures.
- PHB: The first bullet is very tempting since you don’t need to Shove the target prone to get Advantage on attacks. But remember that making your target prone also gives them Disadvantage on attacks against you, so Shove is usually a good idea anyway. The second bullet is only useful if you’re facing a single enemy, but even then you’re also negating Advantage/Disadvantage for both yourself and your target, so you’re doing this purely to help your allies in a way that you could accomplish just as well with Shove. This feat is bad. Don’t take it.
- TCoE: +1 to an ability score, one skill proficiency, and Expertise in one thing. Unless you’re planning a rogue dip you almost certainly need Skill Expert to master grappling.
- PHB: The ability to grapple as a Bonus Action is tempting, but you need to hit the target with an attack first, so this adds an additional point of failure. It’s more efficient to go straight to the grapple+shove combo then save attacking for when you have Advantage.
- SCoC: If you’re going to be grappling, you almost certainly want to be proficient in Athletics without resorting to spells, but if you’re reading this article because your party suddenly needs to grapple something that they’re not prepared to handle, this might be your best bet. Tragically it has a range of “self” so your casters are likely the ones about to get handsy.
- PHB: Advantage on Strength checks (really any one ability, but we care about Strength right now), and you can upcast it to target multiple creatures if you need some help.
- PHB: More effective for grappling than Enhance Ability, but less versatile for other purposes. Increasing your size to Large (especially if you started at Small) allows you to grapple creatures up to Huge size, and Advantage on Strength checks is excellent. Unfortunately the 1-minute duration makes this more costly and more difficult to pre-cast than Enhance Ability.
- PHB: A familiar can use Help to give you Advantage, but most grapple builds can’t easily get Find Familiar and won’t have the spell slots to re-cast it when someone blows up your familiar.
- PHB: Not a great option in combat usually, but I’ll never complain about another +1d4. Guidance is amazing, just not as a tool for grappling.
- PHB: The easiest way to impose Disadvantage on an ability checks. Minimum 1-hour Duration with Concentration, and you can move it once you kill your current target. If you have an ally who can cast this for you, that will work just as well as you casting it yourself.
- XGtE: Expertise as a spell. It’s high-level and requires Concentration, so it’s costly. For the cost I would go for Enhance Ability first in most cases.
- Coiling Grasp Tattoo: This works similarly to how monsters grapple: You hit a creature with an attack or ability, and they become grappled. It won’t benefit from anything you do to optimize grappling, but you can throw this on any character and you instantly have a passable way to grapple things.
- Gauntlets of Ogre Power / Belt of Giant’s Strength: If you can get an item to raise your Strength, it will often exceed the normal maximum of 20. If you know that a Belt of Giant’s Strength is on the table, you could forgo increasing Strength and leave lots of room for feats.
- Ioun Stone (Mastery): +1 to Proficiency Bonus is great for many characters. If you have Expertise, you get to add +2 to your Athletics check, and if you’re Concentrating on spells the +1 to your Constitution saves is helpful (I hope you’re proficient in Constitution saves if you’re trying Concentrate while grappling). But for a Legendary item, you could get a Belt of Storm Giant Strength.
- Manual of Gainful Exercise: For the same rarity, a Belt of Giant Strength gets you up to 23 Strength. Unless you’re a barbarian planning to single-class all the way to 20, the belt is the better choice.
- Ring of Spell Storing: Depending on your allies, tis is a great way to get helpful spells without actually learning to cast spells. Hex is an easy go-to since it’s only first level, but if you have a helpful warlock in the party, consider Enhance Ability or Enlarge/Reduce instead.
- Stone of Good Luck: +1 to ability checks and saves. A great item numerically for basically any character
- Custom Lineage Barbarian. Take Skill Expert (athletics) as your feat at first level, and start with 18 Strength. That, coupled with Advantage from Rage makes you extremely effective at grappling with little further effort.
- Hexblood Lore Bard. Okay, fine, you want to play a grapple bard for some reason. Hexblood gets you Hex, which is a big help for grappling, but you don’t get Expertise until level 3. Managing ability scores is difficult. Start 14 Str, 14 Dex, 14 Con, and 16 Cha (after ability score increases, of course. Focus on Charisma and use spells to compensate for relatively poor Strength and for the fact that you’re a valor bard. Beg your DM for a Belt of Giant Strength.
- Hexblood Rune Knight Fighter. Hex once per day will only get you an hour of hex, but the Fighter has good AC and proficiency in Constitution saves, so you’re reasonably good at keeping it running. Eldritch Knight will let you re-cast it, but you could also go for Rune Knight and save Hex for especially difficult opponents. Use on the of the Fighter’s numerous Ability Score Increases to get Skill Expert at some point. At 20th level, you have Expertise and you’re capable of making 4 attacks with one Action, turning Huge, grappling literally anything, giving yourself Advantage, giving your target Disadvantage, and dealing ongoing damage from Fighting Style (Unarmed). This is arguably the best you can possibly get at grappling without getting magic items, but other builds might be more sustainable and more playable below level 20.
- Variant Human Artificer. Take Skill Expert (athletics), put your racial increases and the +1 from Skill Expert into Str/Con/Int to get all three to 16 at level 1. Rush Str to 20, then pivot to Int. Levels 1 and 2 will be really dangerous, but once you hit level 3 and you can wear heavy armor things get much easier. Armorer or Battle Smith will both work great here, so choose whichever you prefer. Once you can cast 2nd-level spells, Enlarge/Reduce becomes your go-to spell unless you prefer Enhance Ability. If you find yourself grappling multiple goes, strongly consider casting Sword Burst instead of attacking with a weapon.
- Variant Human Monk. Take Skill Expert (athletics), put your racial increases into Dex and Wis. Rush Wisdom to 20, then pivot to Dexterity. Take advantage of your 10-foot reach with Arms of the Astral Self to try and keep enemies out of their own melee reach.
The vast majority of creatures will grapple player characters by hitting them with an attack, so the most important thing you can do to avoid being grappled is to not be hit by attacks. Raise your AC and look for other defenses if necessary.
Humanoid enemies may still grapple you using the same grapple rules used by player characters. To counter these creatures, proficiency in Athletics or Acrobatics is helpful, but you can also make yourself larger or make yourself immune to the Grappled condition somehow.
Breaking a Grapple
There are three ways to break a grapple:
- Escape the grapple
- Become immune to the Grappled condition
- Move the grappler and their target apart
Escaping a grapple is straightforward. You make a Strength (Athletics) or Dexterity (Acrobatics) check opposed by the grappler’s Strength (Athletics) check or a check against a fixed DC if you were grappled by an attack. Either way, the grappler typically won’t be as optimized as a player character built for grappling, so success should be within reach even if all you have is an appropriate skill proficiency. The problem is that escaping this way takes an Action to try to escape.
Becoming immune to the Grappled condition is hard, but if you can do it, you’re no longer affected by the condition. The most likely option is a spell like Polymorph.
The easiest as most likely way to break a grapple is my moving the grappler and their target apart. This is fairly simple since you usually only need to move one creature or the other 5 or 10 feet depending on the grappler’s reach.
For martial characters, Shove works great, especially if you have Extra Attack. If you shove the creature away, an attempt will cost one of your attacks, so you can either retry or attack with any remaining attacks. The Crusher feat and Way of the Open Hand’s Open Hand Technique both allow you to move enemies just by hitting them, making it easy to break a grapple for yourself or an ally without cutting into your action economy.
For non-martial characters, options like the Telekinetic feat, teleportation spells like Misty Step, or any other form of forced movement can break a grapple, often without a check of any kind.
If you have an ally stuck in a grapple, you can come to the rescue using similar tactics. If you shove either the grappler or the grappled creature away from the other, you can break a grapple. This is great for shoving your party’s wizard out of a grapple with big strong foes who you might not be strong enough to shove (unless you’re optimized for grappling, in which case you might go shove the tarrasque just to show off). If you’re not a grappler, the spells Dimension Door and Vortex Warp can both pull an ally out of a grapple.
The grapple rules are, by default, tipped in the favor of monsters. But with some very modest optimization, you can turn grappling into a powerful tool to get an upper hand in combat. And with a little more work you can become a borderline-unstoppable grapple monster who can pin down even the strongest of enemies, tipping combat dramatically in your party’s favor.